500 WINSTON SECTION RD

Winston, 97496

  • 4 Bed

  • 2 Bath

  • 2978 SqFt

  • 1 DOM

  • Built: 1910

  • Status: Active

$775,000

X

500 WINSTON SECTION RD

Winston 97496

$775000

  • 4 Bed

  • 2 Bath

  • 2978 SqFt

  • 1 DOM

  • Built: 1910

  • Status: Active

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Krishna Regupathy

Principal Broker

(503) 893-8874

Step back in time without sacrificing modern convenience in this breathtaking 1910 Craftsman home. Nestled among lush orchards & located directly next door to the iconic Brosi Farmstand & Bakery, this estate offers a lifestyle defined by heritage, craftsmanship, & natural beauty. Every inch of this well-maintained home celebrates the Craftsman era, featuring original woodwork, hardwood floors, hand-troweled ceilings, & period light fixtures. The grand entrance features front sitting rooms on both sides, one with a fireplace. Off the hallway is a cozy library/TV room with a fireplace & charming window seat. Choose between the formal dining room for elegant gatherings or the secondary sunlit dining space for casual mornings. The spacious kitchen features a center island & flows into the laundry room equipped with folding station, sink, & outdoor access. The home offers 4 bedrooms & 2 bathrooms, including a primary bedroom with its own fireplace. Upstairs has a large open landing that leads to a secondary sitting room with private balcony overlooking the front yard & orchards. There’s a dedicated office with serene mountain & orchard views. The grounds are designed for both utility & grand-scale entertaining with a historic barn repurposed for weddings, parties, or a gallery. The 3-car garage & ADU includes an attached guest suite, perfect for a high-end Airbnb or multi-generational living. Also included are a large garden shed, storage shed, & woodshed. A circle drive provides ample parking, with gated entrances (one automatic) for secure backyard access. Landscaping includes a built-in sprinkler system & features flower gardens, a tranquil fountain, grape arbor, & boasts 2 apple, 2 cherry, & 1 walnut tree. Relax on the spacious front porch or enjoy the screened-in back porch for bug-free summer evenings. Experience the legacy of one of the area's most distinguished historical homes-offering all the charm of the past without the restrictions of a historical registry.

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Residence Information

  • 1370

  • 1608

  • 0

  • 2978

  • Assessor

  • 2978

  • 3/Gas

  • 4

  • 2

  • 0

  • 2

  • Composition

  • 3, Detached

  • Stories2,Craftsman

  • Driveway,OffStreet

  • 3

  • 1910

  • No

  • LapSiding, ShingleSiding

  • Daylight,FullBasement,Other

  • Daylight,FullBasemen

  • ConcretePerimeter

  • StormWindow,WoodFram

Features and Utilities

  • Dishwasher, Disposal, FreeStandingGasRange, FreeStandingRefrigerator, InstantHotWater, Island, RangeHood, S

  • GarageDoorOpener, HardwoodFloors, HighCeilings, Laundry, SeparateLivingQuartersApartmentAuxLivingUnit, Vi

  • Barn, Fenced, Garden, GasHookup, Gazebo, GuestQuarters, Outbuilding, Porch, Sprinkler, ToolShed, Yard

  • None

  • Electricity

  • ForcedAir

  • PublicSewer

  • Electricity

  • Electricity, Gas

Financial

  • 4087.64

  • 0

  • Cash,Conventional,Other

  • 04-30-2026

  • No

  • No

Comparable Information

  • 1

  • 1

  • Cash,Conventional,Other

  • $775,000

  • $775,000

  • Apr 30, 2026 16:48

Schools

public Elementary : Brockway 2/10 Ratings
public Middle : Winston 3/10 Ratings
public High : Douglas 6/10 Ratings

Map

Listing courtesy of The Neil Company Real Estate.

The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2019 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. Krishna Realty data last checked: May 01, 2026 02:41 | Listing last modified Apr 30, 2026 16:48. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

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